每周分子 | Molecule of the Week

Original ACS美国化学会 ACS美国化学会 2022-07-01

每周分子: ‍反式肉桂醛

Molecule of the Week: trans-Cinnamaldehyde

顾名思义，反式肉桂醛是肉桂油中的天然产物。在自然界中找不到它的顺式对应物；因此，“ trans”的名称经常被省略。

早在19世纪30年代，化学家就报道了通过苯甲醛和乙醛的醛醇缩合反应合成肉桂醛。但是生产它的最经济的方法仍然是通过蒸汽蒸馏肉桂属的树皮。

肉桂醛是食品（例如糖果和饼干）中的重要调味剂，也是香水的增香剂。它也已被用来消灭蚊子幼虫和击退成年蚊子。因为它是自然存在的，所以适合有机农业。

现在换个角度看肉桂醛, 古埃及人(约公元前2600年)用决明子树皮(肉桂)作为杀虫剂来保存木乃伊，并使木乃伊散发出令人愉悦的香气。

肉桂醛信息速览

CAS 登记号	14371-10-9
分子式	C₉H₈O
摩尔质量	132.16 g/mol
外观	黄色油状液体
沸点	250–253 ºC
水溶性	≈1.4 g/L

肉桂醛危害信息

GHS 分类*: 易燃液体，分类4
H227—可燃液体
GHS 分类: 皮肤腐蚀/刺激，分类2
H315—引起皮肤刺激
GHS 分类: 皮肤过敏，分类
H317—可能引起皮肤过敏反应**
GHS 分类: s严重眼损伤/眼刺激，分类 2A
H319—引起严重的眼睛刺激**
GHS 分类: 特定目标器官毒性，单次接触；呼吸道刺激，分类 3
H335—可能引起呼吸道刺激

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社（CAS）提供的SciFinder中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。

trans-Cinnamaldehyde, as its name suggests, is a natural product that occurs in cinnamon oils. Its cis counterpart is not found in nature; thus, “trans” is often omitted from its name.

As early as the 1830s, chemists reported synthesizing cinnamaldehyde via the aldol condensation of benzaldehyde and acetaldehyde. But the most economical way of producing it is still by steam distilling the bark of trees in the genus Cinnamomum.

Cinnamaldehyde is an important flavoring in foods (e.g., candy and cookies) and an odorant for perfumes. It has also been used to eradicate mosquito larvae and repel adult mosquitoes. Because it exists naturally, it is suitable for organic agriculture.

Now for a different take on cinnamaldehyde. It turns out that the ancient Egyptians (ca. 2600 BCE) used the bark of cassia trees (Cinnamomum cassia) as an insecticide to help preserve mummies and give them a pleasing aroma.

trans-Cinnamaldehyde fast facts

CAS Reg. No.	14371-10-9
Empirical formula	C₉H₈O
Molar mass	132.16 g/mol
Appearance	Yellow oily liquid
Boiling point	250–253 ºC
Water solubility	≈1.4 g/L

trans-Cinnamaldehyde hazard information

GHS classification*: flammable liquids, category 4
H227—Combustible liquid
GHS classification: skin corrosion/irritation, category 2
H315—Causes skin irritation
GHS classification: skin sensitization, category 1
H317—May cause an allergic skin reaction**
GHS classification: serious eye damage/eye irritation, category 2A
H319—Causes serious eye irritation**
GHS classification: specific target organ toxicity, single exposure; respiratory tract irritation, category 3
H335—May cause respiratory irritation

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week's molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

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